With its acid colors and slapdash brush strokes, the painting still jolts the eye. The face, blotched in mauve and yellow, is highlighted with thick lines of lime green; the background is a rough patchwork of pastel tints. And the hat! With its high blue brim and round protuberances of pink, lavender and green, the hat is a phosphorescent landscape by itself, improbably perched on the head of a haughty woman whose downturned mouth and bored eyes seem to be expressing disdain at your astonishment.

Man Ray’s 1922 photograph evokes the domestic harmony that Gertrude Stein, seated at the desk, enjoyed with Alice Toklas, standing, who moved into the Steins’ Paris residence in 1910 as her secretary and became her lifelong companion and muse.
(Musée National D'Art Moderne, Centre Georges Pompidou, Paris)

Leo Stein purchased At the Salon: Divan, a brothel scene by Henri de Toulouse-Lautrec, a few years after the painter’s death in 1901. Though Toulouse-Lautrec’s influence was evident in the work of young artists of the day, Leo soon traded his piece for two Renoirs.
(Collection Museu De Arte De Sâo Paulo Assis Chateaubriand, Sâo Paulo, Brazil. Photo by Joâo Musa)

Though Leo lost interest in Picasso, Gertrude embraced his early Cubism, likening it to her writing. Shown here is a postcard from Picasso to Gertrude in 1919.
(Yale Collection of American Literature, Beinecke Rare Book and Manuscript Library)

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If the picture startles even after a century has passed, imagine the reaction when Henri Matisse’s Woman with a Hat was first exhibited in 1905. One outraged critic ridiculed the room at the Grand Palais in Paris, where it reigned alongside the violently hued canvases of like-minded painters, as the lair of fauves, or wild animals. The insult, eventually losing its sting, stuck to the group, which also included André Derain and Maurice de Vlaminck. The Fauves were the most controversial artists in Paris, and of all their paintings, Woman with a Hat was the most notorious.

So when the picture was later hung in the Parisian apartment of Leo and Gertrude Stein, a brother and sister from California, it made their home a destination. “The artists wanted to keep seeing that picture, and the Steins opened it up to anyone who wanted to see it,” says Janet Bishop, curator of painting and sculpture at the San Francisco Museum of Modern Art, which organized “The Steins Collect,” an exhibition of many pieces the Steins held. The exhibition goes on view at the Metropolitan Museum of Art in New York City from February 28 to June 3. (An unrelated exhibition, “Seeing Gertrude Stein: Five Stories,” about her life and work, remains at the Smithsonian National Portrait Gallery until January 22.)

When Leo Stein first saw Woman with a Hat, he thought it “the nastiest smear of paint” he had ever encountered. But for five weeks, he and Gertrude went to the Grand Palais repeatedly to look at it, and then succumbed, paying Matisse 500 francs, the equivalent then of about $100. The purchase helped establish them as serious collectors of avant-garde art, and it did still more for Matisse, who had yet to find generous patrons and desperately needed the money. Over the next few years, he would come to rely for financial and moral support on Gertrude and Leo, and even more on their brother Michael and his wife, Sarah. And it was at the Steins’ that Matisse first came face to face with Pablo Picasso. The two would embark on one of the most fruitful rivalries in art history.

For a few years the California Steins formed, improbably enough, the most important incubator for the Parisian avant-garde. Leo led the way. The fourth of five surviving children born to a German Jewish family that had relocated from Baltimore to Pittsburgh and eventually to the San Francisco Bay area, he was a precocious intellectual and, in childhood, the inseparable companion of his younger sister, Gertrude. When Leo enrolled at Harvard in 1892, she followed him, taking courses at the Harvard Annex, which later became Radcliffe. When he went to the World Exposition in Paris in the summer of 1900, she accompanied him. Leo, then 28, liked Europe so much that he stayed, residing first in Florence and then moving to Paris in 1903. Gertrude, two years younger, visited him in Paris that fall and did not look back.

By then Leo had already abandoned his ideas of taking up law, history, philosophy and biology. In Florence he had befriended the eminent art historian Bernard Berenson and resolved to become an art historian, but he scrapped that ambition, too. As James R. Mellow observed in the 1974 book Charmed Circle: Gertrude Stein and Company, Leo led “a life of perennial self-analysis in the pursuit of self-esteem.” Dining in Paris with the cellist Pablo Casals in 1903, Leo decided he would be an artist. He returned to his hotel that night, lit a blaze in the fireplace, stripped off his clothes and sketched himself nude by the flickering light. Thanks to his uncle, the sculptor Ephraim Keyser, who had just rented a place of his own in Paris, Leo found 27 rue de Fleurus, a two-story residence with an adjoining studio, on the Left Bank near the Luxembourg Gardens. Gertrude soon joined him there.

The source of the Steins’ income was back in California, where their eldest sibling, Michael, had shrewdly managed the business he inherited upon the death of their father in 1891: San Francisco rental properties and streetcar lines. (The two middle children, Simon and Bertha, perhaps lacking the Stein genius, fail to figure much in the family chronicles.) Reports of life in Paris tantalized Michael. In January 1904, he resigned his post as division superintendent of the Market Street Railway in San Francisco so that, with Sarah and their 8-year-old son, Allan, he could join his two younger siblings on the Left Bank. Michael and Sarah took a year’s lease on an apartment a few blocks from Gertrude and Leo. But when the lease was up, they could not bring themselves to return to California. Instead, they rented another apartment close by, on the third floor of a former Protestant church on the rue Madame. They would stay in France for 30 years.

All four of the Paris-based Steins (including Sarah, a Stein by marriage) were natural collectors. Leo pioneered the path, frequenting the galleries and the conservative Paris Salon. He was dissatisfied. He felt he was more on track when he visited the first Autumn Salon in October 1903—it was a reaction to the Paris Salon’s traditionalism—returning many times with Gertrude. He later recounted that he “looked again and again at every single picture, just as a botanist might at the flora of an unknown land.” Still, he was confused by the abundance of art. Consulting Berenson for advice, he set off to investigate the paintings of Paul Cézanne at Ambroise Vollard’s gallery.

The place looked like a junk shop. Although Vollard was resistant to selling pictures to buyers he didn’t know, Leo coaxed an early Cézanne landscape out of him. When brother Michael informed Gertrude and Leo that an unexpected windfall of $1,600, or 8,000 francs, was due to them, they knew what to do. They would buy art at Vollard’s. Established first-rate artists like Daumier, Delacroix and Manet were so expensive that the budding collectors could only afford minor pictures by them. But they were able to buy six small paintings: two each by Cézanne, Renoir and Gauguin. A few months later, Leo and Gertrude returned to Vollard’s and purchased Madame Cézanne with a Fan, for 8,000 francs. In two months, they had spent some $3,200 (equivalent to about $80,000 today): Never again would they lavish so much so fast on art. Vollard would often say approvingly that the Steins were his only clients who collected paintings “not because they were rich, but despite the fact that they weren’t.”

Leo comprehended Cézanne’s importance very early, and spoke eloquently about it. “Leo Stein began to talk,” the photographer Alfred Stieglitz later recalled. “I quickly realized I had never heard more beautiful English nor anything clearer.” Corresponding with a friend late in 1905, Leo wrote that Cézanne had “succeeded in rendering mass with a vital intensity that is unparalleled in the whole history of painting.” Whatever Cézanne’s subject matter, Leo continued, “there is always this remorseless intensity, this endless unending gripping of the form, the unceasing effort to force it to reveal its absolute self-existing quality of mass....Every canvas is a battlefield and victory an unattainable ideal.”

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